These games are a completionists worst nightmare. DO NOT play TES games with a completionist attitude - play it to have an experience. You keep restarting because you feel like you could "complete" things better with a certain type. Stop thinking like that!
Think up a badass character that has downfalls and think up another one. I've never "rerolled" because I never play TES games to win - ultimately that's the goal, but I just use winning as a vessel for having the REAL fun- being able to experience something.
My current guy is a paladin werewolf who specilizes in killing undead and necromancers, but upholds the justice of his faith and his fellow were's. This is who I've chosen to try and build up and to complete the game with (which I always do for my first run). My next character I want to make into the ultimate evil badass mage, who more or less doesn't give two [censored] of the mainquest except to gain the power of dragons. The next one I want to be a kajeet theif who turns to assassination somewhere down the line, and doesn't even start the MQ.
That's how you play these games. You don't play to try and complete things for the best scenario, because you will jsut always reroll. Its not until you start doing the above and start realising that there IS no best path to experience an Elder Scrolls game is when you really start having fun with these games.